N-butyryl-L-Homoserine lactoneA diffusable quorum sensing lactone

N-butyryl-L-Homoserine lactone (CAS 67605-85-0)

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Synonym: C4-HSL; N-Butyryl-L-homoserine lactone
Application: A diffusable quorum sensing lactone
CAS Number: 67605-85-0
Purity: >98%
Molecular Weight: 171.2
Molecular Formula: C8H13NO3
* Refer to Certificate of Analysis for lot specific data (including water content).
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N-butyryl-L-Homoserine lactone, quorum sensing is a regulatory system used by bacteria for controlling gene expression in response to increasing cell density. Controlling bacterial infections by quenching their quorum sensing systems is a promising field of study. The expression of specific target genes, such as transcriptional regulators belonging to the LuxIR family of proteins, is coordinated by synthesis of diffusible acylhomoserine lactone (AHL) molecules. N-butyryl-L-Homoserine lactone is a small diffusible signaling molecule involved in quorum sensing, controlling gene expression, and cellular metabolism. The diverse applications of this molecule include regulation of virulence in general, infection prevention, and formation of biofilms.


References

1 Gould, T.A., Herman, J., Krank, J., et al. Specificity of acyl-homoserine lactone syntheses examined by mass spectrometry. J Bacteriol 188(2) 773-783 (2006). 2 Henke, J.M., Bassler, B.L. Bacterial social engagements. Trends Cell Biol 14(11) 648-656 (2004). 3 Diggle, S.P., Winzer, K., Lazdunski, A., et al. Advancing the quorum in pseudomonas aeruginosa: MvaT and the regulation of n-acylhomoserine lactone production and virulence gene expression. J Bacteriol 184(10) 2576-2586 (2002). 4 Pessi, G., Williams, F., Hindle, Z., et al. The global posttranscriptional regulator RsmA modulates production of virulence determinants and N-acylhomoserine lactones in pseudomonas aeruginosa. J Bacteriol 183(22) 6676-6683 (2001). 5 Hoang, T.T., Schweizer, H.P. Characterization of pseudomonas aeruginosa enoyl-acyl carrier protein reductase (FabI): A target for the antimicrobial triclosan and its role in acylated homoserine lactone synthesis. J Bacteriol 181(17) 5489-5497 (1999). 6 Morohoshi, T., Inaba, T., Kato, N., et al. Identification of quorum-sensing signal molecules and the LuxRI homologs in fish pathogen edwardsiella tarda. Journal of Bioscience and Bioengineering 98(4) 274-281 (2004). 7 Luo, Z., Su, S., Farrand, S.K. In situ activation of the quorum-sensing transcription factor TraR by cognate and noncognate acyl-homoserine lactone ligands: Kinetics and consequences. J Bacteriol 186(19) 5665-5672 (2003).

Physical State :
Solid
Solubility :
Soluble in water (10 mg/ml at 25° C), ethanol, DMSO (~30 mg/ml), DMF (~30 mg/ml), and PBS(pH 7.2) (~10 mg/ml).
Storage :
Store at -20° C
Melting Point :
119.53° C (Predicted)
Boiling Point :
428.06° C at 760 mmHg
Density :
1.13 g/cm3 (Predicted)
Refractive Index :
n20D 1.48
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
PubChem CID :
10130163
MDL Number :
MFCD12912262
SMILES :
CCCC(=O)N[C@H]1CCOC1=O

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